Ethanol → HCID 59160601, compound

HRID 1500055Notes

Reaction equation

HRID 1500055 reaction equation
[CH:1]1([C:6]([O:8][CH2:9][O:10][C:11]2[N:16]=[C:15]([NH:17]C=O)[C:14]([F:20])=[CH:13][N:12]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.O.NN>CCOCC>[CH:1]1([C:6]([O:8][CH2:9][O:10][C:11]2[N:16]=[C:15]([NH2:17])[C:14]([F:20])=[CH:13][N:12]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 59160593HCID 59160593, compound

Product 1

HCID 59160601HCID 59160601, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 25 mL vial was charged with (5-fluoro-4-formamidopyrimidin-2-yloxy)methyl cyclopentanecarboxylate (34.0 mg, 0.120 mmol), ethanol (1 mL), and hydrazine monohydrate (23.3 μL, 0.479 mmol). The resulting clear, colorless solution was then agitated on an orbital shaker at room temperature for 45 min. The crude reaction mixture was diluted with Et2O (50 mL) and was washed with saturated aqueous NaCl solution (50 mL×2). The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (11.2 mg, 36%) as a white solid: mp 101-104° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.97 (d, J=3.4 Hz, 1H), 7.44 (bs, 1H), 5.86 (s, 2H), 2.69-2.83 (m, 1H), 1.42-1.91 (m, 8H); MS (ESI) m/z 256 (M+H)+, 254 (M−H)−.

Workup

  1. customThe crude reaction mixture
  2. washwas washed with saturated aqueous NaCl solution (50 mL×2)
  3. dry with materialThe organic was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2beca5766ceb4c5f8878cac88896f30d
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

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